


Imprisoned

by littlefirefly31



Series: Kink/Request Fics [182]
Category: Supernatural RPF
Genre: Dom/sub Undertones, M/M, Mobster Jensen, Organized Crime, Prison Sex, Shy Jared
Language: English
Status: Completed
Published: 2016-01-01
Updated: 2016-01-01
Packaged: 2018-05-10 19:03:30
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,461
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5597305
Author URL: https://archiveofourown.org/users/littlefirefly31/pseuds/littlefirefly31
Summary: <blockquote class="userstuff">
              <p>Prompt: Jensen is an ex crime boss. Muscled and tattooed, cursing and innuendos; he's an asshole. Cue Jared, the guard assigned to his cell. Jared is baby faced, with a blush that rises easily, especially when Jensen makes his sexual comments.<br/>Jared's days are usually spent sitting outside Jensen's cell. He would try to do crosswords or Sudoku to pass the time but it's mostly punctuated by Jensen making his smartass comments. Even though Jensen is pretty cruel and mirthless, he finds it fun making Jared turn that pretty shade of red, and checking out his ass. Besides, it's not like he has anything better to do.<br/>Somehow or the other, he gets Jared into his cell and he fucks him, being a lot gentler than Jared expected him to be, although still rough. Jensen continues being a jackass to him, and Jared continues trying to block him out, but Jensen fucking him becomes a daily thing.<br/>One day, Jared shows up to work and he's taken to a new prisoner; turns out Jensen was transferred to a new prison. Surprised, he finds himself extremely saddened, and a week passes, during which he misses Jensen terribly. One day he's leaving work, and he sees Jensen leaning against the wall.</p>
            </blockquote>





	Imprisoned

**Author's Note:**

> This was a pretty complex prompt, so I hope I got all the aspects you wanted!

**Prompt** : Jensen is an ex crime boss, jailed for murder, robbery, assault; he's a pretty bad person. Muscled and tattooed, cursing and innuendos; he's a fucking asshole. Cue Jared, the guard assigned to his cell.

Jared is baby faced, with a blush that rises easily, especially when Jensen makes his sexual comments. Despite being a prison officer, he has a sweet face, and a lean, lithe body.

Jared's days are usually spent sitting outside Jensen's cell, getting their meals and stuff. He would try to do crosswords or Sudoku to pass the time but it's mostly punctuated by Jensen making his smartass comments. Even though Jensen is pretty cruel and mirthless, he finds it fun making Jared turn that pretty shade of red, and checking out his ass. Besides, it's not like he has anything better to do.

Somehow or the other, he gets Jared into his cell and he fucks him, being a lot gentler than Jared expected him to be, although still rough. Jensen continues being a jackass to him, and Jared continues trying to block him out, but Jensen fucking him becomes a daily thing, something they both enjoy but don't say it out loud.

Until one day, Jared shows up to work and he's taken to a new prisoner; turns out Jensen was transferred to a new prison. Surprised, he finds himself extremely saddened, and a week passes, during which he misses Jensen terribly.

One day, he's leaving work, and he sees Jensen leaning up against the wall, having gotten bail, shrouded in darkness, only visible by the light of his cigarette. He goes over to Jared and confesses that he actually missed his tight ass (although they both know he missed him and not just the sex) and says they should go out. They go for dinner, and Jared goes to Jensen's mansion (crime boss, duh), where they have sex, and Jared falls asleep on Jensen's chest.

I'd really love having Jensen as a really bad, dark person. Like not even saying that as a crime boss he got rid of rapists, as in genuinely just shooting people because they piss him off, or breaking a chef's legs because he messed up their order. He claims he only likes Jared for sex, but he is (surprised with himself and not quite understanding it but) fond of him, and actually likes him. The contrast between Jensen being this terrible person and Jared being a sweet-natured, easygoing boy would be greatly appreciated.

 

* * *

 

Jensen had loathed being in jail at first. He’d created an empire and one stupid mistake and a betrayal of one of his followers had lead to him being trapped in this dungeon. And he’d been labeled as a high profile case, so security was even tougher than average. But he wouldn’t be in here forever, and he spent his days imagining how he would punish the betrayer. No doubt he’d be put in witness protection, but Jensen had friends in high places. The government wouldn’t stop him from torturing a filthy scum who deserved it.

It all changed when Jared Padalecki showed up at his cell. Apparently the old guard quit or something, and Jared replaced him. He looked like he was fresh out of college and his baby face was so tempting. Jensen imagined his innocent pink lips wrapped around his cock or his face blushing so prettily while Jensen fucked his ass. “So what’d you do to be stuck here guarding me?” Jensen asked. “Pretty thing like you?”

Jared blushed and ignored the question, focusing on his Sudoku. Oh, that blush was just _delicious_. He couldn’t wait to see that cute guard bouncing on his dick. He wanted to see Jared lose himself in pleasure and then feel embarrassed about what a slut he was for Jared’s dick. “I love that blush,” Jensen continued. “You’re so innocent. How is someone like you working in a prison? I thought you were a prostitute when they first brought you in. A reward for my good behavior.”

“If you had good behavior I wouldn’t be here,” Jared muttered. His voice was as sweet as his face. He would probably whisper Jensen’s name so nice and desperately. He scribbled something in his Sudoku book and Jensen adjusted himself in his pants. Those nimble fingers would feel good wrapped around his dick.

“I know what you’re like,” Jensen said. “You don’t get as powerful as I am without learning how to read people.” Jared didn’t respond so Jensen continued. “You’re single. You haven’t been with anyone in a while, so you’ve got a lot of built up sexual tension. You’re submissive in bed, a real cockslut I bet.”

“Shut up,” Jared muttered.

“You’re so unconvincing. You live alone and you’re desperate for human companionship, but you’re too shy to pursue a relationship.” Jensen smirked. “And you hate it, but I turn you on. I bet you’ve jerked off to the image of me fucking you, huh Jaybird?”

“Fuck you.”

“I think you have our roles reversed,” Jensen corrected. “I’ll be fucking _you_. And you’ll come and come until you can’t anymore.”

“Do you ever shut up?” Jared snapped.

“Oh, you can’t blame me. I haven’t had a pretty boy like you in a while. It’s nice to have a bit of eye candy, that last guard didn’t do anything for me.” Jensen reached out through the bars to touch Jared and he jumped away quickly, blushing deeply. “Tell you what: once I’m out of here I’ll come get you. I’ll let you stay with me and fuck your tight ass all day every day. Would you like that?”

Jared concentrated furiously on his crossword with his back to Jensen, but he could see the tips of his ears pink up. Jensen’s new habit was jerking off loudly and right next to the bars; sometimes his come would land on Jared. Jared always blushed that pretty blush and Jensen imagined all the dirty stuff they would do together. When Jared opened the gate to give Jensen his food, the ex-mob boss hauled Jared in and closed the door. Jared was hulking and strong and could probably overpower Jensen, but every part of him screamed submissive and probably _wanted_ Jensen to take control. Sweet little boy, fresh out of college, and delightfully fuckable. “Look, I’ve been in here for months and the most relief I’d had is my own hand. I’m hot, you need a cock in your mouth or ass or somewhere, and I can give you that. Don’t fight too much and I’ll even make it good for you.”

Jared looked scared and his eyes kept glancing towards the door. “This is happening,” Jensen declared. “If you roll over like the bitch I know you want to be both of us can get something out of it. If you struggle I’ll still come but you definitely won’t. Unless you like it like that.”

Jared was practically shaking, and Jensen tried another tactic. He stroked one of Jared’s arms gently and eased him onto the bed. “Just lie down on your stomach, Jared. I’ll take care of you.”

Jared was tense and Jensen knew the tenser he was the worse it would be—for both of them. He rubbed his ass cheeks and bent down to rim the younger man. He ate Jared out until he was whimpering and pliant, gently rubbing his hips against the bed. Jensen narrowed his eyes and slapped Jared’s ass. “I decide when you come, not you sweetheart.”

Jensen used spit and fingers to open Jared open, then shoved his dick in forcefully. Both of them arched and Jensen immediately started to fuck him. “You ever had anything inside here, bitch? Or are you a sweet little virgin, always wanting but never getting?”

“F-fingers,” Jared replied shakily. The metal bedframe was clanging against the stone wall. “But no c-c-cock.”

“Shit, your humiliation is just turning me on,” Jensen groaned. He knew exactly how to thrust to his someone’s prostate, and when Jared squeaked Jensen knew he found it. He hammered against it, his hole sucking down Jensen’s dick. “Jesus, you need a cock in you at all times. You wanna be my little bitch, Padalecki? Do you want to suck me and let me pound your tight ass?”

“Please,” Jared choked. “Please, need to come!”

“Hump the bed,” Jensen ordered. “That’s how you get to come!”

Jared immediately started to rub against the uncomfortably sheets and soon his body was shuddering with an orgasm. Jensen fucked his lax body until his come filled Jared’s ass. He pulled out and watched it drip down Jared’s thighs; it would dry and become an uncomfortable reminder of their dirty tryst. “Clean up and get back outside,” Jensen ordered.

Jared did as he asked on shaking legs, running a hand through his sweaty hair. He looked humiliated and ashamed, but Jensen knew he’d be back in his bed soon.

The next day Jensen taught Jared to put those cocksucking lips to work and give Jensen one of the sloppiest blowjobs he’d ever had. The innocence was incredibly arousing and Jensen discovered his bitch got turned on by Jensen spewing humiliating language at him, shaming him and telling him that all he was good for was a mouth, a tight asshole, and a willing body. He called Jared a bitch and a slut and watched his huge cock twitch and come every day. The shame always burned Jared’s face was he walked or crawled out of Jensen’s cell, and the next day he was back for more, rolling over and spreading his legs.

*

Jared showed up at work one day, preparing himself to see Jensen’s beautiful face, his dirty, persuasive tongue and tried to school his emotions. Every day he’d promised himself he wouldn’t get into Jensen’s bed and failed every time, the allure of orgasms with the sexy crime boss too tempting. Jensen was right—Jared was weak and craved affection, demeaning as it was. Every pump of Jensen’s hips, every stroke of his hand was addicting and Jared couldn’t wait to bury himself in Jensen’s body.

But it wasn’t Jensen in the cell, it was a bulky, overly-tattooed _thug_. “Where’s Jensen?”

The night guard shrugged. “Transferred. High-security prison, little devil was too much for this place I guess.”

Jared didn’t expect his heart to break over a man who degraded him daily, but Jared suddenly couldn’t focus on anything else.

*

A week passed, then two, then a month. Prisoners came and went but none of them lived up to Jensen and their insults didn’t do anything to him. Jensen had called him worse than any of the other criminals and soon they gave up when Jared didn’t react. He felt angry and sad, and jealous that Jensen had probably found a new bitch at the new prison.

When the night guard arrived to relieve him Jared sulked out the door, going home to microwave something and pass out with the aid of alcohol, per usual. Leaning against the wall, looking as cool as ever, was Jensen Ackles. _His_ Jensen. He was almost entirely shrouded in darkness, the light cinders of a cigarette illuminating just his perfect face. “Jensen…”

Jensen smirked. “Hello again, Jared. Out for good behavior, can you believe it? Turns out even the toughest judges aren’t immune to money if you name a price high enough. In this case the price was a couple million and the life of a little girl.”

Jared gulped. He knew Jensen was dangerous, but this just confirmed it. “You—what do you want?”

“I thought I might take my bitch out for a nice dinner and then back to my house for a good fuck. Are you still going to be my good bitch, Jared?”

Jared nodded furiously. “Please.”

“Great.” He tucked a strand of hair behind Jared’s ear. “I missed that sweet little ass. No one else compared. Let’s get a move on.”

Dinner was _lovely_ , Jensen ordered them both wine and steaks that melted in your mouth. Jared hadn’t ever had a meal this luxurious, and for dessert Jensen fed him bites of chocolate cake. Jared felt so safe, even though he was probably safer back in the prison than out in public with Jensen.

Jared was full and tipsy when they left the restaurant and then Jensen fucked him hard back at the house. His mansion was enormous, ridiculously enormous, and Jensen had an array of sex toys that he used on Jared. The cock ring was his favorite, and kept his ass stuffed with vibrators and clamps on his nipples before fucking him, denying him orgasm for hours. He found all the sensitive spots, eating out Jared until he came and sucking on his balls, a particularly arousing sensation. He was wrung out by the end of the night and passed out on Jensen’s chest, the crime boss’ hand running through his hair.

*

Jensen found himself feeling _protective_. In the bedroom he used Jared’s ass until it was raw and sore, spanked up until he couldn’t sit, and bruised every inch. But he was the only one that was allowed to turn Jared black and blue, the only one to fuck that tight hole and use that hot mouth. He always reminded Jared that all he wanted was sex, but the idea of anyone hurting Jared made him want to slit some throats. He was an expert in getting the most torture out before the victim finally died, and made good use of his talents to work out the energy. Jared was an adorable puppy dog, and Jensen could play him like a fiddle. He found himself feeling even fond of the boy. Normally he kicked his sexual partners out right after the orgasms, not caring how or if they got home, but Jared fell asleep on his chest or under his arm each night.

They were sweating and panting that night, Jared on all fours with a vibrating cock ring and a ball gag in his mouth, Jensen’s cock pounding at his hole. “Thank god I found you,” Jensen groaned. “Don’t know what I’d do without this ass. Love having a little sex kitten at my house, don’t even have to try anymore.”

Jared moaned in the gag and Jensen thrust inside powerfully. “That’s all you’re good for, you little slut. You’re here for sex and nothing else, understand?”

Jared nodded, frantically humping the air. Jensen undid the cock ring and immediately his come spurted on Jensen’s nice, white carpet. When his own orgasm exploded he pulled out and left Jared on the ground to clean himself off.

Jensen hauled himself naked into bed, but left some space on the right side for Jared. 

**Author's Note:**

> i'm overwhelmed with the lovely prompts you've all left, so I'm not accepting anymore prompts until I have a handle on them. Thanks for your understanding!


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